Tetrahydrofuran → Acetic acid, (((methylamino)carbonyl)amino)oxo-, butyl ester

Participants

Reaction Steps

8.5 ml of oxalyl chloride was added to 200 ml of tetrahydrofuran, 9.2 ml of butylalcohol was added dropwise for 30 minutes with stirring in an ice-water bath, and the solution was stirred for a hour in an ice-water bath. 7.4 g of methylurea was slowly added thereto and the solution was stirred for 15 hours at room temperature. After tetrahydrofuran was distilled off under the reduced pressure, water was added to the residue and extracted with ethyl acetate. The ethyl acetate layer was washed three times with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The crude product was passed through a column of silica gel. Ethyl acetate was distilled off, and ether was added thereto. The precipitate was filtered off and recrystallized from ethyl acetate-hexane to give 11.2 g of 5-methyloxaluric acid butyl ester (compound 20).

Provenance & Evidence